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Aug 14 / The BALD BULL

#37 Your IPO gains didn’t vanish—they just fueled an insider’s brokerage account.

Your IPO gains didn’t “mysteriously” vanish—they just got pumped into a yacht tank with the word IPO painted on the side and a Wall Street suit at the helm. While you were busy believing the roadshow hype, insiders were circling lock-up expiration day on their calendars like it was Christmas morning. This isn’t just about one stock—it’s about a game they’ve been running for decades. In this post, you’ll discover how lock-up periods really work, why they create predictable profit windows, and exactly when to strike before the insiders cash their chips. If you don’t know this playbook, you’re not trading—you’re tipping. Read on before your next “breakout” ends up buying someone else’s boat fuel.

So.. you bought 
the shiny "New IPO?"


Congrats!

You just bought the Wall Street equivalent of a brand-new sports car… before the first oil change.

Here’s the part they “forget” to mention while they’re ringing the opening bell: The real owners—the founders, VCs, and early employees—are sitting in the pit lane, strapped into Lambos made of your future sell-off, counting down to the lock-up expiration like it’s New Year’s Eve in Vegas.

And when that clock hits zero?


Balloons don’t drop. 

Shares do.

Because nothing says “thanks for the moonshot” like dumping millions of insider shares onto the market and watching retail bag-holders pretend it’s a “healthy pullback.”

In Time Freedom Trading, we don’t just watch the confetti fall—we front-run the hangover. 

We know when the insiders get itchy trigger fingers, we know where the liquidity will thin, and we know how to fade the lock-up like it’s a bad TikTok trend.

So buckle up. 

We’re about to walk you through the What, So What, and Now What of IPO lock-up fades—so next time, you’re not the exit strategy… you’re the sniper.

Since 1980, nearly 60% of U.S. IPOs have underperformed the market three years after listing — and the median underperformance is around –18% relative to the S&P 500."


| Source: Jay R. Ritter, University of Florida IPO database

"Wall Street IPOs aren’t golden tickets—they’re more like scratch-off lotto cards… with the odds printed in invisible ink.”

IPO LOCK-UPS 

WHAT IS IT? 

What Is the IPO Lock-up Period?

An IPO lock-up period is a contractual restriction—typically lasting 90 to 180 days—during which insiders (founders, employees, early investors) cannot sell their shares following the IPO. It stabilizes supply after listing, avoiding immediate flood sales and overly volatile pricing. It’s not mandated by regulators but agreed upon between the issuing company and underwriters, and the terms are detailed in the IPO prospectus.

What Happens When It Expires?

Once the lock-up ends, insiders may begin selling, increasing supply and exerting downward pressure on the stock price. Empirically, stocks often decline 1–3% right after lock-up expiration; over the following month, the average drop can be around 2.4%, though larger firms tend to see a milder 0.5% decline 

Trader behaviors—like building short interest in anticipation of selling pressure—often begin leading into the expiration.

SO WHAT? 

Why Traders Care?

  • Anticipated Selling Pressure: Unlocking of shares can flood the market with supply, potentially triggering price dips.

  • Volatility Opportunities: The period around lock‑up expiration typically brings increased volatility—ideal for nimble traders.

  • Technical Dynamics: Thin float issues (e.g., when only a small portion of shares are tradable) can amplify price swings, both before and after the expiration.

Surprising Statistic 
(That Will Ruin Someone’s Day)

Despite the fireworks on day one, the long game is a different story:

  • From 1980–2023, U.S. IPOs delivered an average 3‑year market‑adjusted return of –20.2%—that’s a 20% underperformance compared to just staying in the broader market (like the S&P500)


  • So while insiders are busy topping off their yacht fuel tanks, retail investors are left holding the under-performing pump.

Key 2024–2025 Update

If you thought that trend had reversed recently, think again:

  • A 2025 analysis of IPOs since January 2024 shows two-thirds of them are already trading below their listing price—barely off the starting line and already in a hole.


TIME FREEDOM TRADING VIEW

In TFT speak: Your IPO gains didn’t vanish—they just dodged you and ended up in the Cayman account of someone wearing a suit.

Example IPO : 
CoreWeave (CRWV)

The Q2 Earnings Report  for CRWV downgraded future expectations with Michael Intrator, Co-Founder and CEO of CoreWeave comments that included;

  • "the market is underestimating the "thematic power of more compute, sooner – more powerful, larger fabrics at gargantuan scale".

  • Intrator stresses that scaling CoreWeave's capacity and services is critical to its success in a market he describes as "structurally undersupplied".

  • Since its March 2025 IPO, the AI-cloud firm soared nearly 200%. Its lock‑up is set to expire immediately after a recent earnings report.


  • Impact: Analysts warn of possible selling pressure, though historical data suggests very little immediate impact on the first day—meanwhile, a moderate decline (~2.4%) over the next month is more common.


  • Its large float and market cap (~$57B) suggest a smaller average post‑lock‑up decline (~0.5%) relative to smaller IPOs 

NOW WHAT? 

Strategies: What to Know & What Not to Do

What to Know:

  1. Prospectus Details Are Key
    • Review IPO S‑1 filings for exact lock‑up dates and share volumes subject to lock-up.

  2. Monitor Historical Behavior
    • Look at how similar companies reacted around lock‑up expirations—especially in your sector.

  3. Watch Insider Incentives
    • Not all insiders immediately sell. Strong insider retention may signal confidence and mitigate downside.

  4. Consider Supply vs. Float Size
    • If a large share percentage is locked, expiration is more impactful. A small locked float may mute effects.


What Not To Do: 


  • Don’t ignore lock‑up dates—even if the stock still looks “hot.”


  • Avoid assuming lock‑up expiry always leads to dramatic declines—it’s often subtle or priced in.


  • Don’t trade without gauging liquidity; thin float can lead to excessive slippage.



When Is the Sweet Spot to Fade?

  1. Short Window Before Expiry
    • As pressure mounts heading into expiration, some traders take short positions or buy put options anticipating a pullback.
  2. Day of Expiration
    • Market pricing already adjusted? Expect volatility; traders may either short or look for reverse moves if a short squeeze occurs—e.g., Shake Shack once rallied 30% post-lock-up due to a squeeze.
  3. 1–4 Weeks After Expiry
    • Historically, this is where the average 2.4% drop materializes; for larger firms, keep expectations moderated (~0.5%) .
  4. Post Volatility Stabilization
    • If insiders hold, or company fundamentals remain strong, stock might regain strength—observe whether insiders hold or sell at expiry.

Summary Table

PhaseTypical Price ReactionStrategic Approach
Pre-expiryGradual sell anticipationBuild cautious short positions, or hedge
Expiration DayMixed outcomes; volatileMonitor for squeeze or breakdown
Weeks After Expiry~2.4% avg drop (0.5% for large)Consider adding shorts or buying dips
Post-Vol StabilizedSentiment-driven reboundAssess fundamentals for long entries

Recent IPO Examples in 2025

Tactical Trading Plan

Here are some of the standout IPOs this year—the kinds of names where savvy fade strategies could come into play:

  • Bullish (BLSH) – Crypto exchange priced at $37, soared as much as 218% on debut (August 13, 2025)
  • Miami International Holdings (MIAX) – IPO priced at $23 and listed at ~32% premium debut (August 14, 2025)
  • Circle Internet Group (CRCL) – Stablecoin issuer; price exploded from $31 IPO to over $153, now valued around $35B
  • CoreWeave (CRWV) – AI infrastructure firm: lock‑up expiration arriving now, with ~200% IPO rally preceding it.
  • Other names: Figma, Firefly Aerospace, and Chime—all examples of strong IPO runs in 2025.

TLDR:

Fading IPO lock-up periods is a lucrative but nuanced strategy. To sharpen your edge:

  • Do your homework—know the prospectus, locked float, and insider intentions.
  • Time it wisely—short just before expiry, watch volatility early, and target the 1–4 week window for potential mean reversion.
  • Stay nimble and risk-aware—not all drop; some may rebound sharply due to positive sentiment or insider holding.

Bottom line: Long-term holdings should be like an apartment building in your portfolio. You don’t just own it—you collect rent every month. Covered Call Season? That’s when the rent checks get bigger.

“Let us not grow weary in doing good, for at the proper time we will reap a harvest if we do not give up.”

| Galatians 6:9


The market rewards those who respect the process, plant the seeds, and give their trades — and their strategy — the time to grow. Just like a farmer doesn’t dig up seeds to check on them every day, disciplined traders let the power of time and compounding do the heavy lifting. Stay consistent. Stay patient. Your harvest will come.
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So… when is your “when”?


When will you finally build your own Wealth Operating System — the one that pays you whether the market’s running, resting, or throwing a tantrum?

Or will you keep your money unemployed, sitting in the corner scrolling TikTok, while you keep clocking in for a paycheck like nothing’s wrong?

Because here’s the truth: you’re not stuck — you’re just one strategy away from flipping the script. Covered calls are how you start.

Click here and make your money work harder than you do.

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 | The "Bald Bull

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